99604-12-3

Upstream product

• 4545-84-0 trans-2,3-dicarbomethoxybicyclo<2.2.2>oct-5-ene 
• 84258-03-7 trans-2,3-bis(chloroformyl)bicyclo<2.2.2>oct-5-ene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 24327-08-0 meso-endo-tetrahydro-4,7-ethanoisobenzofuran-1,3-dione 
• 57427-48-2 cis-endo-2,3-bis(hydroxymethyl)bicyclo[2.2.2]oct-5-ene 
• 98-59-9 p-toluenesulfonyl chloride 
• 17441-67-7 trans-2,3-bis(hydroxymethyl)bicyclo<2.2.2>oct-5-ene 

Downstream Products

• 92688-78-3 endo-4-thiatricyclo<5.2.2.0^2,6>undec-8-ene 4,4-dioxide 

Relevant academic research and scientific papers

Interaction between Exocyclic s-cis Butadiene and Homoconjugated Functions. Preparation and Diels-Alder Reactivity of Remotely Substituted 2,3-Dimethylidenebicyclooctanes

The preparations of 5,6-dimethylidene-2-exo-bicyclooctanol (8), its endo isomer 9, 5,6-dimethylidene-2-bicyclooctanone (10) and 2exo,3exo-epoxy-5,6-dimethylidenebicyclooctane (11) are described.The kinetics of their cycloaddition to tetracianoethylene has been measured in toluene at 25 deg C together with those of 2,3-dimethylidenebicyclooctane (7) and 5,6-dimethylidenebicyclooct-2-ene (12).The effects of remote substituon on the Diels-Alder reactivity of 2,3-dimethylidenebicyclooctanes are compared with those observed in the 2,3-dimethyl idenenorbornane series (1-6).

Soluble polyacetylene derivatives by chain-growth polymerization of dienes

A new method for the fabrication of soluble polyacetylene derivatives was developed based on bromination-dehydrobromination of bicyclic diene polymers. High molecular weight polymer precursors were synthesized by radical 1,4-polymerization of the corresponding dienes, which contained a bicyclo[2.2.2]octane skeleton. Polymer precursors with narrow molecular distributions were prepared by nitroxide-mediated polymerization of the bicyclic diene monomers. Regioselective elimination from the brominated polymer afforded a polyacetylene derivative contaning bicyclic substituents, which was readily soluble in common organic solvents. The polymer electronic bandgap, obtained by optical and electrochemical measurements, was in the range 1.4-1.7 eV. Low bandgap values were attributed to the conformational inflexibility of the bicyclic substituent forcing coplanar orientation of the backbone double bonds. Solid-state conductivity of the produced polymer in the undoped form was measured to be 1.5 × 10-5 S/m. This new synthetic method allows for the chain-growth production of polyacetylene derivatives that possess favorable electronic properties and superior solubility characteristics to pristine polyacetylene.

Deuterium Kinetic Isotope Effects in the 1,4-Dimethylenecyclohexane Boat Cope Rearrangement

In order to examine the extent of bond making in the boat-like 3,3-sigmatropic shift transition states, trans-2,3-dimethyl-1,4-dimethylenecyclohexane (T) and its exomethylene tetradeuteria derivative (TXD) were prepared.The 3,3-shift of TXD at 305 deg C r